The One Question to Ask Yourself Before Starting a Business

At this point in his career, serial entrepreneur Jason Nazar has developed a one-word litmus test for aspiring entrepreneurs: “Why?”

If you can’t answer that key question, entrepreneurship probably isn’t for you. The 37-year-old has learned as much in his experience as a founder(he sold his document-sharing company Docstoc to Intuit intu in 2013 for a reported $50 million, although Intuit recently shut it down) and as a partner at a venture consulting firm, where he worked with numerous startups.

“When I look at an entrepreneur, I ask, ‘Do they have a huge desire to achieve their goal? And is that desire bigger than the external circumstance they’re facing,’” Nazar says.

After the Docstoc acquisition, Nazar knew he wanted to build something more meaningful the next time around. So he started working on his second act:Comparably, a platform that provides salary data for public and private companies. His “why?”:A desire to encourage open and transparent conversations around compensation.

Nazar spoke with Fortune about some of the biggest lessons he has learned during his entrepreneurial career.

This Q&A has been edited for grammar and clarity.

You’ve already founded and successfully sold a company. Why do it again?

Nazar: I enjoy my time off and spending time with family and friends, but if that’s all I did, I would feel like a waste and a failure. I want to be in a position to take the opportunities that I’ve had and help as many people as possible. I’m not going to be the person who cures cancer. I’m not going to help us get to Mars. But I do really love recruiting and leading a group of really passionate people. At this point, I’ve been around a lot of different companies where I’ve seen the good and the bad. I want to be in a position to look back 10 years from today and say, “We made a meaningful dent in the way companies think about transparency and how they interact with their employees.”

Honestly, people can look at me from the outside and say, “Look, he’s had all of this success,” but you make a lot of mistakes. I wasn’t always the best version of myself as a CEO. Sometimes I would micromanage people, and I would get too stressed out. Over the years, you feel like, “If I could do this all over again with a clean slate and with an amazing group of people, how much better could I be personally, and how much further could I take the company?” I just want to be a better version of myself this time around.

What does it take to be a successful entrepreneur?

Nazar: The first is you have to have a massive “why.” If you don’t have a big burning reason why you’re doing what you’re doing, then you’ll always let the “what” and the “how” be an excuse for not doing that thing. Whereas if you have that big burning “why,” you’ll always figure out the “what” and the “how.”

The second is that you need to have an intense work ethic. There are just too many variables you cannot control. You can’t control what the market’s going to do. You can’t control what the competition’s going to do. But you can always control how much effort you put in. That increases your luckiness. Effort helps you go through more iterations. The more iterations you can go through, the more likely you are to stumble on things, and it then makes it feel like lightning struck or magic happened. The research shows that the vast majority of people who excel in their discipline – whether it’s athletics, music or science – do not actually have any meaningful difference when it comes to IQ or learning ability. It’s that they have a systematic discipline to practice. I fundamentally believe that hard work is what gives anybody the competitive advantage.

The third thing is something people that don’t talk about enough: Soft skills and likeability are big things that people miss when it comes to entrepreneurship.We go through so much of our educational system and we learn facts. We’re not ever taught how to be charismatic, likeable or persuasive. A really big part of being a successful entrepreneur is the ability to get other people to do things for you that are in their best interest. You need to have a social fluidity about you that creates an ease in harsh environments.

What has been the biggest challenge you’ve faced as an entrepreneur?

Nazar: Dealing with other people. What happens as an entrepreneur is that every single thing that happens in a company becomes a reflection of you. Your employees constantly hold up a mirror to you of all of your worst traits and all of the things you do wrong. You can’t complain about your employees because at the end of the day, you hired them. You created the structure of goals where they’re successful or they’re not successful.

Hiring is extremely difficult. Even after this many years, I can’t sit down with someone and have an hour-long conversation and know whether they’ll be a good fit for the company. So the ideal way for me is to say, “Hey, let’s work together for a month,” so we can get to know each other first. The hardest part is finding, growing and retaining really exceptional people and creating an environment where the sum of all the parts is greater than the whole.

To serial entrepreneur Ido Leffler, starting a business is “like a drug.”

Leffler, 38, hasco-founded three businesses: Yes To Inc., a natural beauty-care company, Cheeky, a tableware company, and the school supply brand Yoobi.

Leffler’s passion for entrepreneurship stems from his parents.Born in Israel, he and his family moved to Australia when he was a child. His father had built a successful property development companyand the family had it all – the beautiful home, the comfortable lifestyle. But when Leffler was 12, Australia hit a major recession, and as the residential market collapsed, so did his father’s business. While they lost nearly everything and had to move into a tiny apartment, Leffler’s father refused to declare bankruptcy and vowed to pay back all his debtors. And he did.The experience fueled Leffler’s belief that running your own business can still be worth it despite the massive risks that come along with it.

“I always wanted to be an entrepreneur, but that was a great lesson on how to always be ready,” he says. “It’s essential to build your business under the premise that things can go wrong.”

Leffler also has extensive experience on the other side of the table, namely determining whether emerging startups are worthy of investment dollars. In addition to being an advisor to Birchbox and Levo, among others, Leffler is an active investor in the consumer tech space.

And now, thanks to his role as an angel investor in the new Oxygen Channel show Quit Your Day Job, which premiered on March 30, he can add “reality TV star” to his resume.

At a panel in New York City, Fortune asked him to share some tips for aspiring entrepreneurs.

This Q&A has been edited for grammar and clarity.

You’re a serial entrepreneur and angel investor. What are the three things you look for in an entrepreneur?

Leffler: Everything we do is based on three key pillars – incredible people, kick ass product and awesome cause. We look for someone who truly cares about what they’re doing and someone we believe can drive the business. The product they’re creating must be something more than what you can find in the marketplace. It must be truly differentiated from what’s out there. And there must be an awesome cause – we really want founders who can engage from Day 1 in something that can be really meaningful for the community.

What are some really big mistakes you see first-time entrepreneurs making?

Leffler: First-time entrepreneurs, more often than not, are not focusing on the bottom line. At the end of the day, your business needs to get to a point where it can fund itself. You just can’t expect investors to continuously pour money into it. The other mistake we see entrepreneurs making is creating big, flashy offices. When we set up our office, we literally built our own Ikea furniture. Our first office was a converted mechanic’s workshop. That’s what you want to see. You want to see people taking every cent you give them and treating it like it’s the last cent they’re going to get.

What is your advice for aspiring entrepreneurs – in particular, immigrant entrepreneurs?

Leffler: As a foreigner [born in Israel, Leffler moved with his family to Australia as a child], you see this country as the land of opportunity more than anybody else. I remember landing here thinking, “Oh my God, if I can just get Los Angeles to love my product, that’s more than the entire country where I grew up.”

I personally believe that my accent has helped me in business. It makes you different, and it makes you stand out. So many people try to mask their accent. I think you should be yourself, be articulate and be very observant of the cultures around you. I encourage you to let your accent shine, and it will make you stand out from anyone who’s here in this country.

5 Business Lessons From the 50-Year-Old Company That Made Coffee Cool

When you pioneer an industry, how can you continue to stay disruptive for generations to come? Just ask Peet’s Coffee, the 50-year-old coffee company fighting to stay relevant and appeal to craft coffee-chugging millennials.

Fifty years ago today, Alfred Peet opened the very first Peet’s Coffee shop. The year was 1966, when coffee from a can was the norm. From his shop in Berkeley, Calif., the Dutch immigrant began hand-roasting coffee beans in small batches, creating bold and complex blends that were unlike anything in the American market.

That was the beginning of the specialty coffee movement.

Today, the question at Peet’s Coffee is how to keep ahead of that movement while staying true to its brand. As demand for specialty coffee has exploded, so has the competition.

Peet’s CEO Dave Burwick and Peet’s board member Jerry Baldwin, who was one of the founders of Starbucks, have learned plenty of lessons about entrepreneurship, disruption and innovation over the coffee chain’s decades-long existence. The pair recently sat down with Fortune to share five key lessons entrepreneurs can use as they look to grow their business.

1. Seek out the best players in your field and learn from the ground up.

When starting a new venture, entrepreneurs must know every aspect of their business in and out. And what better way to gain insight than to seek out the most respected industry leader to teach you the ropes? That’s exactly what Baldwin and his business partners, Zev Siegl and Gordon Bowker, did before opening the doors at Starbucks. They realized that the way to get close to the “Moses” of coffee was to work in one of his stores. Baldwin started scooping coffee beans at the original Peet’s store in California. That knowledge helped him when he started Starbucks in 1971; he was the coffee giant’s first roaster. “All of my early coffee knowledge came from Alfred and what we learned there,” Baldwin says. “What was clear to us was [how much] he knew about coffee, how credible he was and how lucky we were to have him share that with us.”

2. Don’t be afraid to make the right decision quickly – and move on.

Some decisions require a great deal of contemplation, but when you’re sure you know the answer, don’t be afraid to act quickly. In 1984, while Baldwin was busy running Starbucks, he found out Peet’s was up for sale. “I had to excuse myself, go to the men’s room and dance,” he says. The decision was easy – he bought Peet’s (which was a four-store chain) and then owned two coffee companies he loved.

A few years later, he had to make another big decision: Bowker, his business partner at Starbucks, decided to sell his share of the company. Baldwin turned to his most trusted confidante – his wife Jane. In a matter of 30 seconds, he decided to sell the company he founded to buy Bowker out — and keep Peet’s. “I knew that no matter how good we would make Starbucks, it would never be Peet’s,” he says.

3. Grow big, grow fast, but don’t grow out of your brand values.

Peet’s still has no plans of chasing Starbucks, which now has 22,000 stores and generates annual revenue of $17 billion. With 240 stores nationwide, Peet’s will bring in about $800 million in revenue by the end of 2016. Burwick’s goal is to increase that number to $2 billion in the next five years.

To do that, Burwick says the company must uphold the quality of its coffee, but “do things differently to grow and to reach more people.” In 2015, Peet’s went on an aggressive buying spree, acquiring third-wave coffee brands Stumptown Coffee Roasters and Intelligentsia Coffee. (Interestingly enough, the founders of both companies got their start at Peet’s.) The acquisitions did not go unnoticed, and devoted coffee lovers sounded off on Twitter. To calm the uproar, Burwick emphasized that Peet’s will keep the leadership in place and allow the brands to operate independently.

The chain continues to abide by a vision of staying small and true to its craft. As Burwick says, it’s about “scaling a company’s smallness.”

4. Give in to the pressure to innovate.

The coffee industry is largely driven by consumer demand for novelty. Right now, cold brew coffee is the hot trend, favored by24% of consumers (most of them millennials).

In May 2015, Peet’s launched cold brew in all of its locations and remodeled its stores to make them more appealing to a younger demographic. The company later bought Stumptown, what it views as the pioneer of cold brew coffee, to further capture the millennial market.

Of course, not everyone is fortunate enough to be able to stay on top of the trends by buying up other companies; the larger message is to have a finger on the pulse of the market at all times and embrace the idea of changing your offerings.

5. Don’t forget what made you great in the first place.

In order for a pioneering company to maintain its dominance in the market, it must experiment with new products, but it must never lose touch with its roots. Burwick and Baldwin see Peet’s age an advantage, not an impediment. The acquisitions, the remodeling of Peet’s coffee shops, the cold brew. It’s all part of the plan to adapt. But perhaps the most disruptive thing Peet’s does today is something that dates back to Alfred Peet’s original store in 1966 – the reliance on human precision to brew coffee.

“We’re still using manual espresso machines in 2016, for crying out loud,” Baldwin says.

How a CEO found her second act

Leaving a startup you’ve led and helped make a success is never easy, but figuring your next act can be even harder. For 13 years, Diane Hessan was CEO of Communispace, one of the first companies to help global brands build and manage online consumer communities. In 2011, she sold it to Omnicom for an undisclosed sum and stayed at the helm as the company grew to more than 600 employees in nine countries.

Hessan officially stepped down in March 2014. In October 2014, she was named CEO of Startup Institute, a fledgling Boston firm that offers eight-week boot camp programs for job seekers hoping to work at startups. Hessan had known Startup Institute because it had used some of Communispace’s spare office space, but she says she never imagined she’d go to work there — and almost didn’t. In a recent interview, she explains why she made the move and her vision for the organization.

Q: Why did you decide to leave Communispace?

Toward the end of 2013, I started thinking that I had been at Communispace for 13 years, had a phenomenal leadership team, and that maybe it was time to give somebody else the chance to see what they could do with the company. As for me, I thought that maybe I had another thing in me and that if I did, it was time for me to get moving on it.

Q: How did you go about deciding what that “thing” would be?

I had a lot of conversations and everyone told me not to take something right away – to take some time to breathe and really see the landscape because if you do that, you’ll have a chance to do something a little more transformative.

So between March and October, I took time to give speeches and be on panels, to do some extra work for the boards I’m on and to just take my time to see what was out there. And I got a lot of offers – from big companies, from non-profits, from early stage startups and from some startups that had gotten funding and were doing really, really well and kind of needed adult supervision. Where the founder was young and hungry and fabulous but not able to run a larger organization and scale it. Those were the ones I was mostly interested in.

Q: How did Startup Institute end up on your radar?

Basically what happened was I narrowing my search and there was another job that I almost took with another early stage company. And I just decide that my heart wasn’t in it. And I called somebody who I knew was familiar with the company and said, “look I’m thinking about turning this down. Am I making he biggest mistake of my life by saying no?” After about half an hour she said, “No, I think you’re making the right decision. But I have another opportunity for you that I think you might be excited about: Startup Institute.”

I went, “oh, you’re kidding!” I got so excited about it right away.

Q: But initially you turned it down. What made you change your mind?

I decided as interesting as it was, it was too early for me to jump. I was still getting a lot of phone calls. With a little bit of regret, I wrote to the [founders of Startup Institute] and said it’s too early for me.

So I moved on and two weeks later, I was having a drink with a friend of mine named Sherri Oberg, who was a CEO who had just had an exit. We were talking about what she should do next. I said, “you know Sherri, I just turned something down and it might be perfect for you.” I started telling her about Startup Institute and she was very interested. So I get back into my car and I’m driving home and I say to myself, “I’ll be damned if I’m going to let Sherri Oberg run that company.”

So I called her and said, “I think that was a really important drink. I think I made a mistake. I think I want that job.” Sherri and I laugh about that now. You have to go with your heart, and all of the sudden I realized what was in my heart.

Q: So where do you want to take the company?

We have this unbelievable product – an eight-week boot camp that gives people the skills and mindset and network that you need to be able to work in a startup or a really high growth company.I think with a company that does what we do, the big risk is that you end up having this absolutely wonderful little program that does great stuff. But if we’re trying to have an impact, the way you do that is to turn it into a business in the best sense of the word. It’s looking at absolutely every element of the program and what we’re trying to do for students. From employee experience to upgrading our curriculum to changing he way we work with our partners, to adding more online learning. We’re trying to turn it into a business that has impact all over the world.

Q: The startup world is known for being a white boys’ club. What is Startup Institute doing to address that?

Diversity is hard-wired into our organization. In our last round of classes in our 5 cities, the students were 41% women and 35% people of color. We also have a scholarship program for women and minorities. And when we open in a new city, we typically reserve at least 5 scholarships for diversity candidates; after all, if our first class of students (and therefore our first alumni) are from a diverse population, it will affect who we attract in the future in that city.

However, our commitment is broader than that. We admit 20% of our applicants, and thus we try hard to create classes that are filled with all colors, all ages, and all points of view. We want our students to learn to think creatively and to collaborate with people who have different viewpoints. That’s a key skill for a growth company employee.

Q: And what’s the verdict on the new job so far?

Now, I would say that 90% of the time I’m having so much fun, and 10% of the time I’m looking in the mirror saying, “Oh my god what I have I done?” Because, here we go again – you’re raising money and you’re dealing with all kinds of issues and trying to make sure you have the right team and trying to figure out how you scale, and trying to make sure you really, really understand what business you’re in – all the things you need to do in the early stage of a company. Here we go again.

Donna Fenn has been writing about entrepreneurship for more than thirty years. She is the author of two books: Alpha Dogs: How Your Small Business Can Become a Leader of the Pack; and Upstarts: How GenY Entrepreneurs are Rocking the World of Business, and a contributing editor at Inc. Magazine.

How getting fired led Hunger Games producer Nina Jacobson to success

There’s an old joke that helps The Hunger Games producer Nina Jacobson survive hard times. You know the one: A kid wakes up on Christmas morning to a pile of manure under the tree—only to excitedly claim that there must be a pony in there somewhere. “I always try to find the pony,” says Jacobson.

Like that time she was unexpectedly let go from her gig as president of Walt Disney’s DIS Buena Vista Motion Picture Group in 2006. Though Jacobson oversaw the first Pirates of the Caribbean film, Remember the Titans, and the first The Chronicles of Narnia film, among other blockbuster hits, she was one of the casualties in a management shake-up. But the firing pushed her to start her own production company.

Jacobson launched Color Force in 2007. The company quickly secured the rights to Jeff Kinney’s Diary of a Wimpy Kid books. The three subsequent films in the series grossed more than $310 million on a total budget of $55 million, according to the movie finance site The Numbers. The first two The Hunger Games films have done even better, pulling in $1.85 billion on a total budget of $210 million. The next installment in the series, The Hunger Games: Mockingjay Part 1, will likely reap a similar windfall when it’s released on November 21. Given that track record, Jacobson hasn’t just found a pony—she’s ridden a unicorn through Hollywood, developing stories that she genuinely loves and turning them into commercial hits.

Despite the large box office numbers, Color Force purposely remains a relatively small operation. It has just seven employees focusing on one to two movies a year. “That gives us the ability to tell someone that they will be one of five projects we have, not one of 50,” says Jacobson.

The low headcount keeps Jacobson busy. On any given day, she will pursue rights to material, find financiers to back projects, meet with studio heads, hire screenwriters and directors, be on a location shoot, assist in film editing or map out a film’s distribution strategy. Her ground-level involvement means that she is fully invested in each project.

“I know that everything Nina submits is something that she knows how to make, who the audience is and how she would ask us to market and sell it,” says Fox 2000 Pictures president Elizabeth Gabler, who worked with Jacobson on Diary of a Wimpy Kid and signed Color Force to a first-look deal this summer. “Everything is completely thought out before she makes a move.”

From a business standpoint, everything has to be. With only a few films in development, Color Force can’t afford to have any bombs. And while it likely earns a handsome payday from The Hunger Games—Color Force has been paid an undisclosed fee for its services and given a share of the profits—those funds don’t last forever for an ambitious, growing company in the fickle film industry.

That unpredictability means attention to detail is crucial. Jacobson’s managerial style has transformed from top-line decision-making on projects already in good shape to sweating projects’ details. “As a studio executive, I took the approach that people are competent until proven otherwise. But when you make a movie, because there is so little time to fix things when they break, you have to almost come to it with the mindset that everyone is incompetent until proven otherwise,” she says. “They usually aren’t, but you have to think, What if this goes wrong? What if that goes wrong?”

“A producer having her level of love of story is pretty rare, “says The Hunger Games director Francis Lawrence. “I think a lot of producers sit in story meetings and have ideas, but I don’t think they are quite as good as Nina’s.”

Jacobson acts as the conduit between the storytellers and the studio, managing costs and editorial concerns and advocating on behalf of what she thinks the film needs. Her background gives her the ability to harmonize the business and the creative sides. “A lot of times people are only able to see one or the other,” says Lionsgate co-president Erik Feig, who oversees The Hunger Games for the studio. “She is one of the rare individuals who has the ability to focus on the forest and the trees.”

Besides The Hunger Games, Color Force has acquired the rights to Where’d You Go, Bernadette by Maria Semple, The Goldfinch by Donna Tartt and Crazy Rich Asians by Kevin Kwan. But first up is a series for FX called “The People Vs. O.J. Simpson,” based on The Run of His Life by Jeffrey Toobin; it’s slated for 2015.

Jacobson’s media diet is voracious and varied. She reads The New Yorker, New York, Texas Monthly and Longreads.com. She listens to “This American Life,” “Radiolab,” UnFictional.” She’s currently watching Orphan Black, Sherlock, Transparent, The Affair, The Leftovers and The Honourable Woman. Her favorite journalists are some of the best out there—Lawrence Wright, Jon Krakauer, David Kushner and Patrick Keefe, the 2014 winner of the National Magazine Award for Feature Writing.

Jacobson’s strong understanding of what makes a compelling narrative resonates with the authors and directors she teams up with on films. “She made me feel very safe [creatively],” says Lawrence, mentioning that even Jacobson’s critiques were welcome. “When she says something about the film, it’s coming from a genuine, smart and tasteful place, and she’s usually right.” (The Hunger Games author Suzanne Collins trusted Jacobson so much that their initial deal was struck verbally over the phone before any formal contracts were written up. “I had such a strong emotional reaction to the book that there was no way she could see that she didn’t have a fan,” says Jacobson.)

As Color Force branches out into TV shows, Jacobson envisions controlled expansion. She’ll add another member or two to the company’s staff and do two to three movies a year. At this size, Color Force can remain nimble—and Jacobson can continue to make project decisions based on her own interests.

“We will always be more of a boutique rather than a factory, but we would like to be a slightly bigger boutique,” she says. “When I became a producer, I told myself I will finally be able to bring my dog to work,” she says of implementing the company’s first (and favorite) perk. “Dogs in the office are very important.”

Former McCain staffers on ditching politics for Silicon Valley

The legions of campaign workers whose candidates lost an election on Tuesday need not necessarily worry about finding their next gig. As other publications have noted, technology companies are more eager than ever to snap up Washington insiders with expertise navigating the Beltway, hiring at a clip that shows losing a campaign can be the beginning of a career in a whole new industry.

Companies from Airbnb to Uber have been poaching political staffers, many of them female, as lobbying legislators and influencing regulators becomes more integral to their businesses.

To name a few: Jill Hazelbaker, the national communications director for John McCain’s 2008 presidential campaign joined Snapchat in October to head the company’s communications and policy efforts (Hazelbaker had previously been Google’s senior director of communications and government relations). Katie Biber, senior legal advisor to Mitt Romney’s 2012 presidential campaign is now in the same role at Airbnb. Niki Christoff worked on the policy side of John McCain’s 2008 presidential campaign before decamping for Google GOOG, where she now heads communications for the East Coast.

But campaigns also seem to attract and develop a certain type of character well suited to Silicon Valley. It’s no surprise that hiring managers look for political experience: both sectors are fast-paced and high-stakes, attracting people who are highly motivated by risk and reward.

“People who work on campaigns tend to be scrappy, to work really hard and to be entrepreneurs,” says Christoff. Women who cut their teeth in the rough-and-tumble world of politics emerge from campaigns uniquely suited to the demanding, stressful and high-risk environment at growing technology companies, she adds.

Despite the public’s focus on Obama’s digitally savvy team, former McCain staffers like Christoff seem plenty appealing to Silicon Valley. Christoff’s colleague Samantha Smith is a manager for Google’s global communications and public policy team, after working on the McCain campaign’s communications team and serving as press secretary to Sen. Richard Burr (R – N.C.) as well as communications director to his 2010 reelection campaign.

Studies have shown that women are less inclined to take financial and career risks, but “with big risks come big rewards,” Christoff says. “People who go into politics have a very high tolerance for risk because fifty percent of the time, you’re not going to win.”

Campaign staffers are conditioned for chaos, which helps develop skills that translate to the breakneck speed of the technology industry, Smith says. Fast-paced, high-growth and closely scrutinized, “political campaigns are the ultimate start-ups,” she says. “Success requires responsiveness to user feedback, in this case the voters.”

The migration from politics to tech, of course, is not limited to women. In September, Uber, the car-sharing service treading piecemeal regional regulations, snapped up David Plouffe, President Barack Obama’s 2008 campaign manager, as its senior vice president of policy and strategy. Facebook FB has made several hires from Capitol Hill, including Joel Kaplan, White House Deputy Chief of Staff for Policy to President George W. Bush—who was promoted last month to the social network’s vice president of global policy. And there’s Tucker Bounds, a McCain campaign spokesperson who left Facebook in September to work on a startup called Sidewire.

Given the spate of hires and promotions this fall, Silicon Valley’s interest in Washington shows no signs of flagging. “Tech and politics at their base level are similar,” Christoff says. “They’re not about money but winning hearts and minds.”

From consulting to consoling

Ask Corey Gordon how old he is and he couldn’t tell you, because he has no birth certificate. His childhood was fragmented, just as his memories of it are.

He says he vaguely remembers an older woman taking care of him in his infancy, but she wasn’t his mother. He remembers being cold and walking barefoot on ice. He remembers going hungry, and being so malnourished that when he coughed, he had to pull worms out of his mouth.

The abandoned child of a Korean woman and an American soldier who met during the Korean War, Gordon was, like so many children of such unions, ostracized. His mother abandoned him, and he might have been forced to survive on the streets had he not been delivered to an orphanage, where he experienced his first shower, food security and kids his own age to play with. He recalls the day an orphanage staffer told him he’d been adopted by a family in Minnesota. “It was a dream come true. All I wanted to be was to be American,” Gordon says.

Adjusting to the dream, and his new surroundings, would be tough for Gordon. “On my first day of school I ran away because I thought I was being given away. My parents had to come with me to school for several weeks so I could realize that I could come home every day,” Gordon recalls.

Over time Gordon settled into life in Minnesota, went on to college Northwestern College in Minnesota, started a family of his own and began a successful career in marketing, mostly for finance and banking companies. In 2003, looking to cut down on travel, he took a job with Americana Capital Corporation, a bank holding company, which owned Americana National Bank, a small asset bank in southern Minnesota. Gordon was hired to help grow the two national subsidiaries ACC had.

It seemed to be the perfect fit, but six to nine months into the job began to hear rumblings of issues the CEO was having with the Office of the Comptroller of the Currency. The issues were concerning to other holdings the CEO had and his alleged use of the bank for his own personal purposes. In the end the CEO was removed from the company was and barred from banking. Gordon was not involved with the management of the bank and was implicated nor charged of any wrongdoing in the matter.

Gordon, who was 36 at the time, was too young to retire from professional life, but the problems at American Capital rattled him. He realized he was seeking more meaning and fulfillment from his work. He began consulting to nonprofit organizations, providing guidance on marketing and fundraising. In 2012 Gordon started his own consulting firm aimed at helping nonprofits, Nonprofit Strategies, and found his services in great demand. But there was one nonprofit that he found himself going the extra mile for: Feed the Children, one of the largest charities in the world.

“I knew some of the guys, so I flew down and met with the executive team and took them on as clients. And before I knew it I was working 50 hours a week, almost double the budgeted 29 hours. I talked with Kevin (Hagan, President and CEO of Feed the Children) and he was like, ‘Why don’t you just join us?’”

So he did. Gordon put his consulting business on hold on Oct. 1, 2012, and became the chief marketing and communications officer of Oklahoma City-based Feed the Children, a faith-based organization that provides food and other poverty relief in the U.S.

Last summer, Feed the Children had the opportunity to open an office in South Korea and Gordon was selected to lead the trip. The office will direct all support and fundraising programs in the country which will most likely include an orphanage, among other things. Gordon expressed some initial hesitation about returning to his native country, but in the end he agreed. The trip was followed last by a trip in December to North Korea on the invitation of Dr. James [Kim, president of Pyongyang University of Science and Technology. (Dr. Kim, featured in Fortune in 2009, also left a life in business to pursue a broader calling, bringing Western-style education to North Korea.)

In Pyongyang, Gordon visited five orphanages to see firsthand the university’s strategies to combat hunger in the poverty-stricken country. Feed the Children is going to begin providing support to the orphanages in the near future. For Gordon, now 47, the visits were at once heart wrenching but also inspiring. “For me, as a former orphan, to go visit those orphanages? Sometimes life can seem like a meandering journey,” he says. After many so twists and turns, Gordon now seems to have found a clear path.

Words of Wisdom

Advice for retirees considering a move from corporate life to giving back “First, do it. You won’t regret it. Second, start by identifying the cause that you’re the most passionate about. There are many good organizations, but given the reality, there will be challenges with all of them. Having the bedrock of a cause you’re willing to invest your life in will keep you energized.”

What he wishes he knew before the switch “I was far too naïve coming into the not-for-profit sector. The nonprofit space is indeed about charity, altruism, passion and doing good, but it’s still human beings managing the organizations and running the programs. I was surprised at how badly nonprofits often treat each other, viewing each other as competitors, when if you look at their vision/mission statements, ostensibly they should be collaborating. If people can check their egos and logos at the door, there’s a tremendous opportunity for real positive change.”

Biggest challenge “Culture shock. These are broad-brush statements, but generally speaking, in the for-profit realm, change can be constant, with market forces and consumers driving new strategies, technologies and products/services. Change is anathema to nonprofits. For-profits play to win, with a focus on risk management. Nonprofits play not to lose, with a focus on risk avoidance. For-profits embrace innovation and R&D, looking for exponential gains. Nonprofits feel hamstrung by the insane fixation on arbitrary overhead ratios, thereby avoiding innovation and R&D, finding safety in incremental gains.”

Biggest reward “Purpose. I look back on my life and see how all of my personal and professional experiences have woven together for a work that takes me far beyond myself. To know that every day I get to wake up and positively impact the lives of children here in the U.S. and around the world that brings a wonderful sense of purpose and meaning for what I do each and every day.”

Next is a series of articles that looks at executives’ efforts to use their talents and skills to enrich or support the lives of others and upon retirement from professional life.

Second Act: Jake Steinfeld and Major League Lacrosse

In November of 1977, Jake Steinfeld, a freshman lacrosse player at the State University of New York at Cortland, was standing on a field in the hail. “What am I doing?” he wondered. It was freezing, and he saw no future in the sport. So Steinfeld — a weightlifting enthusiast since age 13 — dropped out, moved to Northridge, Calif., and became a bodybuilder.

After winning a few small competitions, he moved over to Studio City and fell into a routine: lifting weights in the morning, working as a bouncer at night. Sandra Will, an actress, approached him one day and told him she needed someone to help her get in shape for a commercial. He trained her, she told friends about his services, and word spread. Among many other big names, Steinfeld worked with Steven Spielberg — who later hired him to help Harrison Ford train to play Indiana Jones — and named his company Body By Jake. He offered personal training by appointment, exercise videos, and eventually TV spots.

Steinfeld milked his Hollywood connections, grew the business, and in 1993 launched a 24-hour network, FitTV, with Tim Robertson, son of televangelist Pat. In 1998, Steinfeld sold FitTV to News Corp. NWSA for an undisclosed figure. He had money, recognizable celebrity, and an itch to try a new venture. His mind returned to those freezing lacrosse practices.

He had read about Dave Morrow, an All-American lacrosse player who founded Warrior, a lacrosse equipment and apparel maker. On a whim Steinfeld called Morrow to persuade him to create a professional lacrosse league. No such thing existed. “He just called me out of the blue,” Morrow says. “It was a 310 number so I thought it was one of my old teammates messing with me. When I called back, someone answered and said, ‘This is Craig from Body By Jake,’ and I almost hung up the phone.” Morrow didn’t, and within minutes the gregarious Body By Jake guy had convinced him.

The two former laxers, along with Robertson, funded Major League Lacrosse (MLL) by themselves. But by the end of the first season, in 2000, MLL was out of money, Steinfeld says. The trio scrounged for years. A turning point came in 2004: Morrow sold Warrior to New Balance, and its owner, Jim Davis, bought a controlling stake in the league, saving it.

Today, the league has just wrapped up its 12th season, with its championship match played on August 26 at Harvard Stadium in Boston. While the MLL is growing nicely, many American sports fans still aren’t aware that pro lacrosse even exists. Dave Gross, MLL commissioner, says that’s to be expected — it seems that creating a sports league from scratch is not easy. “We are not going to be an overnight success,” he says, “but nothing in sports happens that way. We’re not the NFL; we’re not even the MLS at this point. But we’re growing it in the right way.”

Mike Stone, a midfielder for the Boston Cannons (2011 champions), says recognition isn’t why the players are in it anyway. “Right now, with the state of the MLL, you’re doing this because you love the sport,” he says. “We all know nobody is making a killing at it, and it’s a grind for everybody.” Indeed, pros make only $13,000, on average, per season; thus they all have regular jobs. The season is short — 13 weeks — and falls in summer. Still, guys like Stone get paid to do what they love, all thanks to Steinfeld, whose name graces the playoffs trophy.

The Body By Jake boss is now focusing his time on beefing up the league’s size and reach: He helped launch the program Inside the MLL, which began airing this season on CBS Sports Network. He has people working on technology that will make it easier for a casual fan to watch the sport. TV footage will now highlight the player who has the ball, much like in video games, and akin to what Fox tried to do with pro hockey when it highlighted the zooming puck in the late 90s.

The MLL has sponsorship deals with beverage bigs like Powerade, Coke Zero, and Bud Light. This year two expansion teams debuted: the Charlotte Hounds and the Ohio Machine. The latter, in a June game against the Denver Outlaws, pulled a crowd of 30,128, the biggest in MLL history. And it will continue to expand: The MLL plans to add two more teams in Florida, Texas, or Atlanta by 2014. After that, it’s shooting for four new teams on the West Coast, which would bring the total to 14.

“We’re getting close,” Steinfeld hopes, “to the tipping point.” And Hollywood still beckons: Lionsgate bought Take a Shot!, a book by Steinfeld and Morrow about creating the league, with plans to make it into a TV Drama series.

On starting a company

Dive in. “Don’t get ready, don’t get set. Just go,” Steinfeld says on starting his league. “Sometimes the smartest people are the most paralyzed.”

Find people you trust. “People you know will always have your back, not when you’re standing on top of the mountain but in the deepest ditch.”

Constantly adapt. “Keep reinventing yourself; that’s the only way you survive. Also, it’s important for your sanity.”

A shorter version of this story originally appeared in the September 24, 2012 issue of Fortune.

Bruce Lisman left Wall Street to try to fix Vermont’s economy

Bruce Lisman’s first job on Wall Street, in 1970, was as a file clerk. “Red in red, yellow in yellow, blue in blue,” says Lisman, now 65. “It didn’t take a college education, but I did it anyway.”

It proved a good foundation. At Loeb Rhoades & Co., the University of Vermont graduate and Burlington native made sales assistant, then rose to analyst at Lehman Brothers.

In 1984, Lisman (pronounced LISS-man) became research director at Bear Stearns and then co-head of global equities in 1987, staying until 2009, a year after J.P. Morgan JPM bought Bear. But Lisman eventually decided that nearly 40 years in finance was plenty. He resolved to try something new and moved back to his home state with his many millions.

He wasn’t sure what the new thing would be. So he asked everyone he knew to introduce him to people in Vermont. His interest was meeting as many people as he could. In the course of 18 months he met 400 of them for dinner or a quick cup of coffee. Lisman interviewed them about what they do, why they love it, and why they do it in Vermont. “No one turned me down,” he says. “But some of them I had to convince: ‘Look, I’m not selling insurance. I just want to get some insight.'”

Lisman eventually realized he was getting a broad look at Vermont’s economy. That knowledge informed his new self-funded venture, Campaign for Vermont (CFV), a 501(c)(4) advocacy group that stands for “commonsense ideas” to improve the state’s economy. The group was launched the day after Thanksgiving with 22 founding partners and two founding officers, including a former state finance commissioner under Howard Dean. Lisman has been vague about specific policy goals but is critical of Vermont’s property tax and its current energy plan. From January to March he pumped at least $210,000 of his own money into CFV, $194,000 of it going to advertising.

Barbara O’Connor, a lawyer and former federal public defender, is “hopeful Lisman’s private-sector experience will make Vermont a place where new businesses are welcome.”

Some Vermonters question the group’s true purpose, and local press has portrayed Lisman as a fiscal conservative looking to take on the state’s incumbent Democrats. But Lisman insists CFV is nonpolitical (though its structure is the same one used by Karl Rove and others) and that he does not plan to run for office. He is also writing a book on some of the 400 people he met, focusing on entrepreneurs. It sounds like a lot of work — but for a lifelong Wall Streeter, it probably constitutes a break.

Keys to launching your career

Don’t waste people’s time. “They’ve carved out 30 or 60 or even 90 minutes for you, so try to engage them in good conversation,” says Lisman. “You see enough people and you’ll notice certain characteristics, entrepreneurial at all levels.”

Keep having fun. “Man, is this fun,” Lisman says, “engaging with people who want to engage in debate or ask why one thing works and one doesn’t. In the world to come, which seems pretty unpredictable, citizens need to help each other.”

Free time is for family. Lisman’s new life lets him spend more time with his daughters; one is getting a doctorate in violin performance, the other a master’s in museum education. “I think they can identify more with CFV than what I was doing before.”